N,N,N',N'-Tetramethylazodicarboxamide → Tert-butyl-dimethyl-{4-[2-(2-{2-[2-(2-trityloxy-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-phenoxy}silane

HRID 2075631Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2075631
[C:1]([O:20][CH2:21][CH2:22][O:23][CH2:24][CH2:25][O:26][CH2:27][CH2:28][O:29][CH2:30][CH2:31][O:32][CH2:33][CH2:34][OH:35])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(P(CCCC)CCCC)CCC.[Si:49]([O:56][C:57]1[CH:62]=[CH:61][C:60](O)=[CH:59][CH:58]=1)([C:52]([CH3:55])([CH3:54])[CH3:53])([CH3:51])[CH3:50].N(C(N(C)C)=O)=NC(N(C)C)=O>C1(C)C=CC=CC=1.C(OCC)(=O)C>[C:52]([Si:49]([CH3:51])([CH3:50])[O:56][C:57]1[CH:62]=[CH:61][C:60]([O:35][CH2:34][CH2:33][O:32][CH2:31][CH2:30][O:29][CH2:28][CH2:27][O:26][CH2:25][CH2:24][O:23][CH2:22][CH2:21][O:20][C:1]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[CH:59][CH:58]=1)([CH3:55])([CH3:54])[CH3:53]

Komponenten

7

Edukt 4

HCID 4278N,N,N',N'-TetramethylazodicarboxamideHCID 13831TributylphosphineHCID 5973884-(tert-Butyldimethylsiloxy)phenolHCID 54298879Tr-PEG6

Produkt 1

HCID 23080801Tert-butyl-dimethyl-{4-[2-(2-{2-[2-(2-trityloxy-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-phenoxy}silaneAusbeute 60,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittel3×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of Compound 2 (2.8 g, 5.8 mmol) in toluene (10 ml), a solution of tributylphosphine (1.17 g, 5.8 mmol) in toluene (2 ml) was added at room temperature; this was followed by stirring for 1 hour. This was gradually added to a solution of Compound 18 (1.1 g, 4.9 mmol) and 1,1′-azobis(N,N-dimethylformamide) (1.0 g, 5.8 mmol) in toluene (10 ml), and this was followed by overnight stirring at room temperature. Ethyl acetate was added; the resulting insoluble matter was removed by Celite filtration, and washing was conducted with ethyl acetate. The combined organic phases were concentrated under reduced pressure; the residue obtained was purified by silica gel column chromatography (Yamazen YFLC Gel, eluent (n-hexane:ethyl acetate 2:1)) to yield Compound 21 (colorless oil 2.03 g, 60%).

Aufarbeitung

  1. waitthis was followed by overnight
  2. stirringstirring at room temperature
  3. customthe resulting insoluble matter was removed by Celite filtration
  4. washwashing
  5. concentrationThe combined organic phases were concentrated under reduced pressure
  6. customthe residue obtained
  7. customwas purified by silica gel column chromatography (Yamazen YFLC Gel, eluent (n-hexane:ethyl acetate 2:1))

Quellen und Nachweise

ORD-Eintrag
ord-156eef2c73ff44e1ba6cf4d2404bf72f
Quelldatensatz
uspto-grants-2011_04
Patentnummer
US07919653B2

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